Mineeal



Patented Nov. 25, 1941 were;

as ara r OFFICE M AL bill coMPosI'rroN Jolie; Wasson, Union, and WarrenM. Smith, Elizabeth, N.1J.', assignors to Standard Oil i rDevelopmentCompany, a corporation of Dela- Aware ii-li f txmvention :relates to animproved mineral oil compositionrf The invention is more pafiliqllarly-rconcerned-with a-petroleum oil compositlOIl'QOmPrisingagrelativelysmall amount of a substanceselected from the class oftertiary alkylaromatic -mono-lethers which are characterized by havingat least two alkyl groups attached directly to the aromatic nucleus, oneof which is a .terti ary:alkyl group andwthe other of which i 4 mapcontaining-at 'least two carbon ato sinthemoleculem;

,lt is well known the art to, improve the general quality; and;,-particular -characteristics :of miner l Li. i: p rticu a y p troleumoils, y adding thereto, various; organic. inhibiting agents. Thesematerials SCIYQtO, increase the ability of theqoilto withstand-;operating conditions .under would normallyfail in a relatively short lne nelEiOd-x; ;We have now discovered 'a class fubstances whichareparticularly dee, asaddition agents for petroleum u materials, serve "toproducean oil' blend pressures. The inhibiting agents of our invention?are gtertiary alkylr; aromatic mono-ethers whioh are characterized byhaving-at least :two alkyl groups a mlc euazan hichris a tertia y alylgroup nd; theme wh c is; n k :s Q taining at least two carbon atoms inthe molecule.

T ese mate ial wmaysbe;rep esented by the followingptructural-iormula;I,

m which lt represents a. area-yawn group, Rf represents an' 'alkylgroup-' 'containin'g' at least =twd carbon+atoms in the molecule; and

- "ar repr'esents hydrogen or: "additional amy groupsiBreferred-substances are thos'ein which the tertiary 'alkyl group 7attached directly to the arolrlatio*1uicleus is in the :ortho positionand-"the al yl group having atleast two'earboiratomsan ttacheddirectly:; ,to the varomatic dstabilltywhich will not deteriorate 4nder-,1 IQQSRSWBIB, operating-te p r r and NoDrawlngQjApplicationJanuary 25, 1940,

' Serial No.315,521

a c aims. (Cl. 252-52) the molecule is in the para position with respectto the ether linkage. Materials of this class are, for example, tertiarybutyl ether of ortho tertiary butyl para isopropyl phenol, tertiary amylether of ortho tertiary amyl para isopropyl phenol, tertiary amyl etherof ortho tertiary butyl para isopropyl phenol, tertiary hexyl ether ofortho tertiary hexyl para isopropyl phenol, tertiary butyl ether ofortho tertiary butyl para isobutyl phenol, tertiary butyl ether of orthotertiary butyl para ethyl phenol, tertiary butyl ether or ortho tertiarybutyl para normal butyl phenol, tertiary butyl ether of ortho tertiarybutyl para normal hexyl phenol, and the like. Particularly desirableinhibitors are those in which the tertiary alkyl group attached to theether linkage contains from four to five carbon atoms in the molecule,examples of which are tertiary butyl ether .of ortho tertiary butyl paraisopropyl phenol, tertiary butyl ether of ortho tertiary butyl paraethyl phenol, and tertiary amyl ether of ortho tertiary butyl para ethylphenol. It is also desirable that both alkyl groups attached directly tothe aromatic nucleus contain from four tofive carbon atoms in themolecule.

These materials may be used to improve the quality of any mineral,animal, or vegetable oils, but are particularly desirable for use inpetroleum oils which are employed under severe operating conditions ofelevated temperatures and pressures. The quantity of inhibitorusedwillvary considerably, depending upon the particular inhibitoremployed, the'character or the base oil, as well as upon the'conditionsunder which the oil is to be used. The quantity of inhibitor used mayvary in the range from 0.01% to as high as 3%. However, in general, itis preferred to use from 0.05% to 1.0% of the inhibitor;

In order to further illustrate the invention, the following example isgiven which should notv be construed as limiting the invention in anymanner whatsoever: l

Robinson color 17 grown terially'improved the quality of the petroleum011 v to which they were added.

oil was measured by the Staeger oxidation test.

The results or these tests were as follows:

stances of the present invention are particularly adapted for improvingthe quality ot petroleum lubricating oils, they likewise may be employedfor the stabilization of petroleum hydrocarbons generally against,oxidation, deterioration, and the like, as for example, for thestabilization of Hours Hours 100 Hours 200 Hours 300 Hours450 Neut.Neut. Neut. Neut. Neut. Color No. Color No. Color Color Color Turbineoil 17 0.03 6 0. 30 Black Turbine oil+0.l% tertiary but-El ether ofo-tertiary butyl p-isopropyl g enol l7 0. 03 l7 0. 03 0. (B 12 0. 03Turbine oil+tertiary butyl et er oi ortho tertiary butyl para ethylphenoL 17 0.03 17 0. 03 15 0. 03 12 0. 03 9 Turbine oil+tertiary butylether of ortho W tertiary butyl para normal butyl phenol. l7 0. 03 -170. 03 15 0. 03 12 0. 0:! Turbine oil+tertiary butyl ether of orthotertiary butyl para normal hexyl phenoll7 0. C6 1 l7 0. 1B 12 0. 05 6 0.30

The neutralization number is equivalent to milligrams oi po assium Fromthe above datait is clearly apparent that the" compounds of the presentinvention ma- Further tests were conducted with the following results: 77

- Hours 0 Hours 100 Hours 200 Color 22? Color ggy Color 33? Turbineoil+o terti- 1 sry butyl para iso- 35 propyl phenol 17 0. (B 9. 5 0. l 50. 35 Turbine oil+o-tertisry butyl para ethyl phenol 17 ,0. 03 6 0. 14 30. 45 Turbine oil+o-tertir ary butyl para nornnl butyl phenol. 17 0.03 70. l2 4 0. 40 4o Turbine oil-i-o-tertiary butyl para norml hexylphenol... 17 0. 03 10 0. l2 6 0. 30

From the above it is apparent that the corresponding phenols areineflective. Additional testswere run using relawd substances not withinthe scope of the present invention with the following results:

HouIs'O Hours 100 Hours 200 Color Color Color Turbine -oil+0.17

methyl ether of or 65 the tertiary butyl pars cresol V 17 0. 03 6 0. 30Turbine oil+0.1% oi ethyl ether of ortho tertiary butyl para cresol 170. 03 7 0. n) Turbine urn-0.1%

normal butyl ether 0i ortho terthry butyl pars cresol--- 17 0.03 =7 0.20'lurbineloilfil'ygisov DMD! e 0 orthe tertiary butyl pars cresol l7. 0.03 8 0. l0 Turbine oil+0.l%isov methtglrtoilortho rs cresol ...'Z l7 ,0.03 6 0. 26 Turbine oi1+0.l%secoudsry'butyi ether of ortho terthry,butylparscresol--- 11 our 0 cos s an From the above data it is apparentthat the above substances do not materially aid the quality oi thepetroleum oil.

Itistobeunderstcod-that althoughthesub-- 'Staeger oxidation test: 200cos. of oil are placed in a 400 ccs. beakerand maintained at a tern tureoi C. in the ce ofa metallic eoppercetslyst for various time periods.The color oi the oil is observed m order to determine the quantityoiacldic materials formed. The color was measured by the Tag Robinsoneolorimeter.

hydroxide per gram of oil.

petrolatums, petroleum waxes, motor fuels,

the produd neutralized the like, as well as for the stabilization ofvarious vegetable and animal oils.

The process of the present invention is to be limited by any theory ormode 01' operation; but only in and by the following claims in whichitisdesired toclaim allnoveltyinsoiarasthe prior art permits.

We claim:

1. Composition comprising an oil and a small v amount of a substanceselected from the class of tertiary allryl aromatic mono-ethers whichare characterized by having at least two alkyl groups attached directlyto the aromatic nucleus,. one

of which is a' tertiary alkyl group and the other 0! which isanalkylgroup'containing at least two carbon atoms in the molecule. I

' 2.- Composition comprising a petroleum hydrocarbon and a small amountof a substance-sc lected from the class oi! tertiary alkyl aromaticmono-ethers which are characterised by having at least two alkyl groupsattached'directly to the aromatic nucleus, one of which is a tertiaryalbl group and the other of which is an aikyl group containing at leasttwo carbon atoms in the molecule.

3. Composition in accordance with claim 2 in which the tertiary kylgroups contain from tour to five carbon atoms in the molecule.

4. Composition in accordance with claim 2 in which the alkyl groupscontain from four to live carbon atoms in the molecule.

'againstoxidationcomprisingapetroiemnoilboiling in the lubricating oilrange and a small amount or a substance selected from the class ortertiary alkyl aromatic mono-'ether'swhicharecharacteriaedbyhavingatleasttwoalkylgroups attached directly to thearomatic nucleus. one or which is'a tertiaryalkyl group andthe other ofwhichis'analkylgroupcontaining atlealttwo carbon atomsinthemolecule.

- JOKE I. WABBON.

